I've got a friend who's an actor. She works enough to have her SAG card and get health insurance through them. She gets commercials primarily, but has had nothing going on since the pandemic, so I asked to go and do some mid-week day drinking.

Honestly, we both showed up looking a bit like slobs. I was in joggers and she was also in athletic wear that isn't the kind you wear around Los Angeles to be seen in. She still looks good. But she always looks good. She's about my height with a very tight body that reveals at certain times that she's a little older than she admits to being. Also, I'd never seen her without her roots dyed. I actually find grey hair quite sexy, but I know her line of work so I get it.

Anyway, we're talking about her breakup. She's saying that he was really more of a fuckboy than a boyfriend, but she'd been exclusive with him for a while, she still has some of his shit at her place that they have to see each other again to sort out - you know, standard breakup things.

After a while the conversation turns to sex (as it always does with us) and she's asking me about red light windows in Amsterdam and other parts of Europe. I give her the whole rundown:
-Don't linger too long.
-Don't take pictures.
-Standard rate as long as I've known it is 50 Euros for 15 minutes.
-Be upfront and establish that you're getting a blowjob and multiple positions for your 50 Euros before you enter.
-If you're a client, be respectful and hygienic.

She's letting her mind wander. Her cheeks blush before she starts to crack a smile and says something like: "It sounds so interesting, I'd love to try it."

And I'm like: "As long as it's truly at-will work, I don't see anything wrong with it. If it weren't for COVID I'd say try getting paid for sex every so often if you're going to have it anyway."

Her: "Yeah, that's not something I'd risk right now."

Me: "You wanna roleplay it?"

Her: "What?"

Me: "I could stand outside on your balcony and you could advertise yourself to me from behind the glass in something sexy. Hell, if you want to make the experience more authentic, I'll actually pay you."

Her: "Uh... sure."

_____

We get to her place and I walk out onto the balcony, and before I slide the glass door closed I tell her to make sure she wears a two-piece, and that if she wants to act like a pro, she's got to put the condom on with her mouth.

She points and winks at me as I close the glass door and I pull out my wallet. I've only got 20's and because we hadn't actually talked price I assumed we would use $50 as a stand-in for 50 Euros. Well I've never asked for change from a sexworker and Venmo didn't seem like it would get the feel right. So I took out 60 and moved it to my front pocket.

After a couple minutes of leaning on the railing and looking down at the empty swimming pool, I hear a knock on the glass and I turn around to see her in this ridiculous neon green bra and panty set. I chuckle, and she buries her head in her hands and turns around to laugh off the nervous embarrassment before turning back to me lock eyes and run her hands down her body from her neck to her hips.

I raise two fingers like I'm hailing a taxi and she slides the door open, leaning against it, really showing off her curves.

Her: "Hey baby, you like?"

Me: "I do." I take the money out and show it to her. "So will this get me 15 minutes and multiple positions?"

She takes it and counts it. "Yeah. Follow me."

I'd never been to be bedroom before. I've never fucked her before. But I didn't expect her room to be as much of a mess as it is. I told her to move everything off the bed and onto the floor as I started to undress.

I lay on the edge of the bed looking up at the ceiling and she crawls onto the bed between my legs with a condom in her mouth. She tears it slowly and tosses the wrapper, bringing the condom to her lips and expertly drops her mouth on my cock, unfurling the condom perfectly and pulling it down to the base of my shaft with her fingers, which she leaves in place and grips the base of my dick hard.

I probably neglected to mention that she's got a very big mouth. Not like big lips, but more if Jim Carey was a really sexy woman.

Anyway, she's just gripping the shit out of my base and bobbing her mouth on my head that I say something like "ohshit ohshit ohshit" and burst immediately.

She's like: "Well that was easy."

And I'm like: "I don't know what the fuck happened. Can you give me like 10 minutes and we can go again?"

I get up with my condom still on and pull another $40 from my wallet. "I'll pay for the additional time."

Her: "Look I'm wet as fuck and I need to be fucked. If you can get it up, I need to get off."

Me: "No, I'm running over, you should be compensated appropriately. Also, you're supposed to clean me up."

She looks down at my condom and grabs my dick with one hand and takes the money with the other. She slaps the money down on a dresser or something and pulls the condom off slowly and holds it up to my face. "For an additional 20, I'll drink all of this."

I gave her another 20.

I never fully lost the erection, but I still thought I needed another minute when she sucked the last drop out and slipped her panties to the floor. She leaned in and whispered in my ear "come on."

It probably wasn't the smell of cum on her breath that had me ready to go, but I told her to get me a new condom and get to work.

I'm on my back in seconds and she's lowered herself on me almost as soon as my head hits the mattress. I'm nearly back to full capacity and she's riding me with her back arched and her eyes closed like she's in a fucking audition. It's full on lip biting, hands tugging on her hair, grunting and whining.

Finally her mouth opens and she's gasping. She manages to get her bra off. It drops on my stomach and with what seems to me like her last bit of strength she pulls my hands to her tits and I squeeze them hard right as she collapses on me. She's panting and twitching.

I whisper in her ear: "I still need to cum a second time."

Her: "Mmmm hmmm."

Me: "Yeah, I paid for the second orgasm."

Her: "Okay, take me however you want. I'm sorry, I'm just a little spend and can't help too much."

Me: "Can I cum in your ass?"

Her: "Oh fuck, please cum in my ass."

I don't know why. Must have been the impatience, but I immediately flip her on her back and throw her legs over my shoulders. I first penetrate with the condom on - hoping the lubricant from her pussy will help to open her up a bit, but she's still tight as hell.

Eventually I get my head in her ass and hold it for a bit, getting her comfortable with my girth. After a minute or so I pull out and take the condom off. I break the rules a little and swirl my cock head around her pussy to lube up again and plunge back in her ass.

She's like the tightest pocket pussy you could imagine. I'm pounding her at a medium rate, but it's like my cock wants to pop in and pop out with maximum friction with each thrust. I swear I saw her drooling.

Eventually she breaks character and uses my name when she says: "Fuck ________! Cum in my ass!"

I obliged.

I let my dick pulsate in her for a bit and then pulled out and washed it off in her bathroom. She was still laying on the bed and breathing heavy as I got dresses.

After the final shoelace was tied I said "Hey, thanks a lot for that," and locked the door on my way out.